CN106540631A - A kind of cation Gemini surfactant containing ester group and its preparation method and application - Google Patents
A kind of cation Gemini surfactant containing ester group and its preparation method and application Download PDFInfo
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- CN106540631A CN106540631A CN201610548888.1A CN201610548888A CN106540631A CN 106540631 A CN106540631 A CN 106540631A CN 201610548888 A CN201610548888 A CN 201610548888A CN 106540631 A CN106540631 A CN 106540631A
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- 0 C*(*(*)(**(*)[N+]([O-])OC=C)NN*(*)(**(**)[N+]([O-])OC=C)N)=C Chemical compound C*(*(*)(**(*)[N+]([O-])OC=C)NN*(*)(**(**)[N+]([O-])OC=C)N)=C 0.000 description 1
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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Abstract
The invention discloses a kind of cation Gemini surfactant containing ester group, belongs to surfactant field, which is the compound with structure shown in formula A：Wherein R represents C8～C20Alkyl.Present invention also offers the preparation method of the surfactant, with long-chain bromoalkane, dimethylamine and alkyl methacrylate as raw material, Jing additive reaction and quaternary amine salinization reaction are prepared.Contain ester group in the surfactant molecule so as to can be environmentally friendly with natural degradation.The raw material that the preparation method of surfactant is related to simultaneously is easy to get, and low cost, synthetic method are simple, and synthesis condition is gentle, and the yield and purity of products therefrom is higher.The surfactant is applied to into fracturing fluid field, the prepared viscoelastic surfactant fracturing fluid that obtains has excellent heat-resisting property and stability.
Description
Technical field
The present invention relates to a kind of Gemini surface active agent and preparation method thereof.More particularly it relates to a kind of contain ester
Cation Gemini surfactant of base and its preparation method and application.
Background technology
Aqueous fracturing fluid is broadly divided into：Natural plants fracturing fluid, cellulose fracturing fluid and synthetic polymer hydrofracturing fluid.
Above-mentioned several fracturing fluid systems, at home and abroad each oil field is widely used, and obtains good effect of increasing production.But use
There is common defect in these fracturing fluid systems, be exactly after fracturing liquid rubber-breaking residue will remain in crack, remain in crack
Polymer by the serious permeability for reducing proppant pack, so as to injure payzone, cause fracturing effect to be deteriorated.
The novel water-based fracturing fluid of the class non-polymer that late 1990s develop successfully solves these and asks
Topic.Due to wherein not containing polymer, adsorbance of the residue with proppant filling tape in fracture faces is significantly reduced, form high
The crack of flow conductivity.It is only 30%～45% that field experimentation shows that the row of returning of guar gum fracturing fluid leads, and such non-polymer pressure
Split liquid and the proppant stages permeability retention rate of sand filling is taken typically more than 90%, and will not leave behind filter cake.Therefore, to stratum
Pollution level is less, improves the seepage flow situation of proppant packed layer and Reservoir Fracture, so as to increased Oil ＆ Gas Productivity.It is this
New Fracturing Fluid is non-polymer system, is also clean fracturing fluid or non-injury fracturing fluid, viscoelastic surfactant fracturing fluid.
In surfactant, Gemini surface active agent is by coupling base by two hydrophilic groups and two hydrophobic group
Roll into a ball the new surfactant of a class of connection.Compared with traditional surfactant, Gemini surface active agent can be more
The surface tension of water is effectively reduced, with lower critical micelle concentration, higher absorption property and peculiar aggregation row
For, therefore Gemini surface active agent, especially cation Gemini surfactant received in fields such as tertiary oil recovery, sterilization, printing and dyeing
To the extensive concern of people.
But existing cation Gemini surfactant complicated process of preparation, especially prepare containing amide groups, ester group,
The Gemini surface active agent of the linkers such as ether, it usually needs use more than 100 DEG C of high temperature and the step of complexity, and make
Standby raw material is difficult to obtain so that preparation cost is expensive.Therefore need a kind of synthesis material badly to be easy to get, synthetic method is simple, synthesize bar
Part is gentle, at a lower temperature just can be with obtained cation Gemini surfactant.
The content of the invention
It is an object of the invention to the technique in the presence of overcoming existing cation Gemini surfactant technology of preparing is multiple
Miscellaneous, synthesis condition is harsh and product above-mentioned deficiency disagreeableness to environment, there is provided live on a kind of cationic gemini surface containing ester group
Property agent.
It is a further object of the present invention to provide a kind of preparation method of above-mentioned surfactant.
It is a further object of the present invention to provide purposes of the above-mentioned surfactant in terms of fracturing fluid is prepared.
In order to realize foregoing invention purpose, the invention provides technical scheme below：
A kind of cation Gemini surfactant containing ester group, which is the compound with structure shown in formula A：
Wherein R represents C8～C20Alkyl.
Above-mentioned C8～C20Alkyl refer to the alkyl of the straight or branched with 8～20 carbon atoms, it is preferable that R is represented
The alkyl of 10～20 carbon atoms, it is further preferred that R represents the alkyl of 12～18 carbon atoms, it is highly preferred that R represents 12
The alkyl of～18 carbon atoms, most preferably, R represents the straight chained alkyl of 12～18 carbon atoms.
The preparation method of the cation Gemini surfactant containing ester group of the present invention, comprises the following steps：
S1, first dimethylamine is mixed with alkyl methacrylate, add water, carry out additive reaction, obtain mixed liquor I；
S2, by the mixed liquor I evaporation, be dried, obtain intermediate tertiary amine II；
S3, the intermedium tertiary amine II is mixed with long-chain bromoalkane, add acetone, carry out quaternization reaction, obtain
Mixed liquor I II；
S4, the mixed liquor I II freezing and crystallizing is obtained into surfactant IV.
Above-mentioned alkyl methacrylate is with CH2=C (CH3) COOR structures compound.
Above-mentioned intermediate tertiary amine II is the compound with structure shown in formula B,
Above-mentioned surfactant IV is the compound with structure shown in formula A,
Wherein R represents C8～C20Alkyl.
Preferably, above-mentioned alkyl methacrylate and the mol ratio of dimethylamine are 1: 1～1: 4.It is highly preferred that above-mentioned first
Base alkyl acrylate is 1: 2～1: 4 with the amount ratio of the material of dimethylamine.
Preferably, in above-mentioned steps S1, the reaction temperature of additive reaction is 20～80 DEG C, and the response time is 8～24 hours.
It is highly preferred that the reaction temperature of additive reaction is 20～60 DEG C in above-mentioned steps S1, the response time is 10～18 hours.
Preferably, above-mentioned long-chain bromoalkane is with R1The compound of-Br structures, wherein R1Represent C8～C20Alkyl.
Preferably, in above-mentioned steps S3, long-chain bromoalkane and the mol ratio of intermediate tertiary amine II are 1: 1～4: 1.More preferably
Ground, long-chain bromoalkane are 2: 1～4: 1 with the mol ratio of intermediate tertiary amine II.
Preferably, in above-mentioned steps S3, the reaction temperature of quaternization reaction is 20～80 DEG C, and the response time is 8～24 little
When.It is highly preferred that the reaction temperature of above-mentioned quaternization reaction is 20～60 DEG C, the response time is 10～18 hours.
In above-mentioned steps S2, evaporation, drying steps can be completed in two steps；Can also be completed with a step, such as using rotation
Vaporizer is under low pressure by mixed liquor I evaporation, dry, the acquisition intermediate tertiary amine II.Preferably by rotary evaporator
Under low pressure by mixed liquor I evaporation, dry, the acquisition intermediate tertiary amine II.
Application of the cation Gemini surfactant containing ester group of the present invention in fracturing fluid, by above-mentioned surfactant and
Counter ion salt is mixed and made into fracturing fluid, and wherein surfactant and the mol ratio of counter ion salt are 1: 2～3: 1, surfactant
Account for the 1～5% of fracturing fluid gross mass.
Preferably, described in above-mentioned fracturing fluid, counter ion salt refers to the thing that can ionize out negatively charged ion in aqueous
Matter, such as salt, such as sodium salt, potassium salt, ammonium salt, at least one of calcium salt；It is highly preferred that the counter ion salt be sodium salt and/or
Potassium salt；Most preferably, the counter ion salt is one or more in sodium salicylate, sodium benzoate, Sodium Chloride and potassium chloride.
Compared with prior art, beneficial effects of the present invention：
The present invention with long-chain bromoalkane, dimethylamine and alkyl methacrylate as raw material, Jing additive reaction and quaternary ammonium salt
Change reaction and prepare a cationoid gemini surfactant, contain ester group in the surfactant molecule so as to can be with
Natural degradation, it is environmentally friendly；The raw material that the method is related to simultaneously is easy to get, and low cost, synthetic method are simple, synthesis condition temperature
With the yield and purity of products therefrom is higher.The surfactant is applied to into fracturing fluid field, it is prepared to obtain viscoelasticity table
Face activating agent fracturing fluid has excellent heat-resisting property and stability.
Specific embodiment
With reference to test example and specific embodiment, the present invention is described in further detail.But this should not be understood
Scope for above-mentioned theme of the invention is only limitted to below example, and all technologies realized based on present invention belong to this
The scope of invention.
Embodiment 1
Methacrylic acid positive ten diester and dimethylamine are dissolved in into water, and are reacted 24 hours at 20 DEG C, obtain mixed liquor 1I,
Positive ten diester of methacrylic acid is 1: 1.5 with the mol ratio of dimethylamine；Under low pressure mixed liquor 1I is steamed using rotary evaporator
Send out, be dried, obtain intermediate tertiary amine 1II；The intermediate tertiary amine 1II for obtaining and glycol dibromide are dissolved in into acetone, and 20
React 24 hours at DEG C, obtain mixed liquor 1III, intermediate tertiary amine 1II is 2: 1 with the mol ratio of glycol dibromide；Will mixing
Liquid 1III freezing and crystallizings obtain surfactant 1IV.
The surfactant 1IV is the compound with structure shown in formula 1A,
The potassium chloride of 3% surfactant 1IV and 1% is dissolved in into water, viscoelastic surfactant clean fracturing is obtained
Liquid, temperature resistance reach 67 DEG C.The method of testing of the heat-resisting property is documented in standard " SYT 5107-2005 aqueous fracturing fluid performances
In evaluation methodology ".
Embodiment 2
Methacrylic acid positive hexadecyl ester and dimethylamine are dissolved in into water, and are reacted 12 hours at 50 DEG C, obtain mixed liquor 2I,
The positive hexadecyl ester of methacrylic acid is 1: 2 with the mol ratio of dimethylamine；Under low pressure mixed liquor 2I is evaporated using rotary evaporator,
It is dried, obtains intermediate tertiary amine 2II；The intermediate tertiary amine 2II for obtaining is dissolved in into acetone with glycol dibromide, and at 60 DEG C
Reaction 12 hours, obtains mixed liquor 2III, and intermediate tertiary amine 2II is 2.5: 1 with the mol ratio ratio of glycol dibromide；Will mixing
Liquid 21II is freezed and is recrystallized to give surfactant 2IV.
The surfactant 2IV is the compound with structure shown in formula 2A,
The sodium salicylate of 3% surfactant 2IV and 2% is dissolved in into water, viscoelastic surfactant cleaning pressure is obtained
Liquid is split, temperature resistance reaches 97 DEG C.The method of testing of the heat-resisting property is documented in standard " SYT5107-2005 aqueous fracturing fluid performances
In evaluation methodology ".
Embodiment 3
Methacrylic acid positive octadecyl ester and dimethylamine are dissolved in into water, and are reacted 8 hours at 80 DEG C, obtain mixed liquor 3I,
Methacrylic acid positive 18 is 1: 4 with the mol ratio ratio of dimethylamine；Under low pressure mixed liquor 3I is evaporated using rotary evaporator,
It is dried, obtains intermediate tertiary amine 3II；The intermediate tertiary amine 3II for obtaining is dissolved in into acetone with glycol dibromide, and at 80 DEG C
Reaction 8 hours, obtains mixed liquor 3III, and intermediate tertiary amine 3II is 4: 1 with the mol ratio of glycol dibromide；By mixed liquor
3III freezing and crystallizings obtain surfactant 3IV.
The surfactant 3IV is the compound with structure shown in formula 3A,
The sodium salicylate of 5% surfactant 3IV and 4% is dissolved in into water, viscoelastic surfactant cleaning pressure is obtained
Liquid is split, temperature resistance reaches 120 DEG C.The method of testing of the heat-resisting property is documented in standard " SYT5107-2005 water-based fracturing fluidities
In energy evaluation methodology ".
Although being described in detail to the present invention with reference to specific embodiment, those skilled in the art are come
Say, it is obvious which to be made various changes and modifications on the premise of without departing from the scope.Enforcement described herein
What mode was merely exemplary, which is not limiting as the present invention.The many of the present invention disclosed herein changes and modifications and is
It is possible, and fall into the scope of the present invention.Therefore, protection domain is not limited by description set out above, and which is only
Limited by appended claim, its scope includes all equivalents of claim theme.Each claim is incorporated to
Bright book is used as embodiments of the present invention.Thus, claim is further instruction book, and is that the present invention is preferable to carry out
The increase of mode.The disclosure of all patents referred to herein, patent application and publication is incorporated herein by reference, bag
Include in their the exemplary of offer, program or other detailed supplements.
Claims (10)
1. a kind of cation Gemini surfactant containing ester group, which is the compound with structure shown in formula A：
Wherein R represents C8～C20Alkyl.
2. the cation Gemini surfactant containing ester group according to claim 1, it is characterised in that wherein R represents C10
～C20Alkyl.
3. prepare claim 1 described in the cation Gemini surfactant containing ester group method, it is characterised in that include with
Lower step：
S1, first dimethylamine is mixed with alkyl methacrylate, add water, carry out additive reaction, obtain mixed liquor I；
S2, by the mixed liquor I evaporation, be dried, obtain intermediate tertiary amine II；
S3, the intermediate tertiary amine II is mixed with long-chain bromoalkane, add acetone, carry out quaternization reaction, mixed
Liquid III；
S4, the mixed liquor I II freezing and crystallizing is obtained into surfactant IV.
4. preparation method according to claim 3, it is characterised in that alkyl methacrylate described in step S1
Mol ratio with dimethylamine is 1: 1～1: 4.
5. preparation method according to claim 3, it is characterised in that the reaction temperature of additive reaction described in step S1
Spend for 20～80 DEG C, the response time is 8～24 hours.
6. preparation method according to claim 3, it is characterised in that the long-chain bromoalkane is with R1The change of-Br structures
Compound, wherein R1Represent C10～C20Alkyl.
7. preparation method according to claim 3, it is characterised in that long-chain bromoalkane described in step S3 with it is described
The mol ratio of intermediate tertiary amine II is 1: 1～4: 1.
8. preparation method according to claim 3, it is characterised in that the reaction of quaternization described in step S3 it is anti-
Temperature is answered for 20～80 DEG C, the response time is 8～24 hours.
9. application of the surfactant as claimed in claim 1 in fracturing fluid, it is characterised in that by the surfactant and instead
Ion salt is mixed and made into fracturing fluid, and the surfactant is 1: 2～3: 1 with the mol ratio of the counter ion salt, the surface
Activating agent accounts for the 1～5% of fracturing fluid gross mass.
10. application of the surfactant in fracturing fluid according to claim 9, it is characterised in that the counter ion salt is sodium
Salt, potassium salt or its combination in any.
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Cited By (4)
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| CN110257043A (en) * | 2019-07-06 | 2019-09-20 | 西南石油大学 | A kind of stimuli responsive type clean fracturing fluid and preparation method thereof |
| CN110257042A (en) * | 2019-07-06 | 2019-09-20 | 西南石油大学 | A kind of reservoir breaks the clean fracturing fluid and preparation method thereof of glue automatically |
| CN115057795A (en) * | 2022-06-23 | 2022-09-16 | 西南石油大学 | Novel temperature-resistant salt-tolerant penta-cation tetra-viscoelastic surfactant and synthesis method thereof |
| US11459499B2 (en) | 2018-12-11 | 2022-10-04 | King Fahd University Of Petroleum And Minerals | Amidoamine-based gemini surfactant containing ethoxylate units and a method for oil recovery |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11459499B2 (en) | 2018-12-11 | 2022-10-04 | King Fahd University Of Petroleum And Minerals | Amidoamine-based gemini surfactant containing ethoxylate units and a method for oil recovery |
| CN110257043A (en) * | 2019-07-06 | 2019-09-20 | 西南石油大学 | A kind of stimuli responsive type clean fracturing fluid and preparation method thereof |
| CN110257042A (en) * | 2019-07-06 | 2019-09-20 | 西南石油大学 | A kind of reservoir breaks the clean fracturing fluid and preparation method thereof of glue automatically |
| CN110257042B (en) * | 2019-07-06 | 2021-06-04 | 西南石油大学 | Clean fracturing fluid for automatic reservoir gel breaking and preparation method thereof |
| CN110257043B (en) * | 2019-07-06 | 2021-06-04 | 西南石油大学 | Stimulus-response type clean fracturing fluid and preparation method thereof |
| CN115057795A (en) * | 2022-06-23 | 2022-09-16 | 西南石油大学 | Novel temperature-resistant salt-tolerant penta-cation tetra-viscoelastic surfactant and synthesis method thereof |
| CN115057795B (en) * | 2022-06-23 | 2024-01-12 | 西南石油大学 | Novel temperature-resistant salt-resistant five-cation four-ion viscoelastic surfactant and synthesis method thereof |
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